Hydrochloric Acid → HCID 18409104, compound

HRID 1586986Notes

Reaction equation

HRID 1586986 reaction equation
[CH3:1][NH:2][C:3]1([CH3:21])[CH2:12][CH2:11][CH2:10][C:9]2[N:8]=[C:7]([O:13]CC3C=CC=CC=3)[CH:6]=[CH:5][C:4]1=2.[ClH:22].[H][H]>C(O)C.CC(O)C.[Pd]>[ClH:22].[CH3:21][C:3]1([NH:2][CH3:1])[CH2:12][CH2:11][CH2:10][C:9]2[NH:8][C:7](=[O:13])[CH:6]=[CH:5][C:4]1=2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 18409092HCID 18409092, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 18409104HCID 18409104, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

5,6,7,8-Tetrahydro-N,5-dimethyl-2-(phenylmethoxy)-5-quinolinamine (6.3 g) in ethanol (500 ml) was acidified to ca pH2 with a solution of hydrochloric acid in 2-propanol. 10% Palladium-on-carbon (315 mg) was added and the mixture was shaken on Parr hydrogenation apparatus, starting at 55 psi of hydrogen, until hydrogen uptake ceased. The catalyst was collected and the filtrate was neutralized with 4-polyvinylpyridine. The solution was concentrated in vacuo to a volume of about 75 ml and diethyl ether was added. The precipitate was collected and recrystallized first from methanol and then from water/2-propanol to afford 1.3 g (25%) of product, mp 190°-195° C. (dec).

Workup

  1. customThe catalyst was collected
  2. concentrationThe solution was concentrated in vacuo to a volume of about 75 ml and diethyl ether
  3. additionwas added
  4. customThe precipitate was collected
  5. customrecrystallized first from methanol

Sources & evidence

ORD record
ord-fb32d60553a34565882ce4bc40030d7e
Source dataset
uspto-grants-1993_06
Patent number
US05216164

Reaction notes

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